GGR, I am almost certain your right on all accounts. Are you a engineer or mechanic?
I am going to study a spare 108 block I have here and figure out which of the bolts down the front face lead into oil passages. Will end up resealing everything but just a good exercise to ensure when it all goes back together that I pay the 'correct' attention to the bolts that actually matter.
I think that my bell housing leak was the same type of issue as well. The box had obviously been taking apart as all the seals were beautifully fresh but something was leaking even when the car was sitting up doing nothing. Pools of oil would form on the garage floor under the bell housing. Logic dictates that the oil isn't from the main front gearbox seal as it sits above the waterline of the gearbox. I am almost certain this applies to the engine oil and the rear main engine seal as well.
So if I have oil continually leaking for weeks on end without starting the car it my humble opinion that the culprit with my gearbox issues is the two lower bolts which penetrate through an open hole into the main gearbox cavity. When I refilled my box I didn't seal these properly and visibly saw oil seeping out. I tipped the box up took the bolts out, cleaned the oil out of the thread with solvent and resealed. I tested the box again by leaving it tipped at a 45 which allowed oil to be constantly flooding all of the front sealing components. Left it overnight to be sure. Dry as a bone. Then turned around the next night and did the same on the rear. I couldn't do it on the top because of the breather which just pisses oil everywhere.
I am wondering how effective thread seal is when you don't clean the thread before use of oil/grease/sludge residue. I know from experience that when I have tried to smear sealing compound on more obvious and accessible mating surfaces which I hadn't cleaned properly that the compound doesn't adhere well at all. I think that perhaps this could be a mistake made by mechanics under time constraints or when the repair is been done in situ and its just too hard to achieve. Bolts just get slapped back in with little thought. Job done, customer pays cash and a couple of months latter the leak begins.
I am really hoping I wont have any more puddles on my garage floor if I pay a little attention at this point of proceedings. Again I am certainly no mechanic but just trying to apply a bit of common sense to the problem. Am 100% certain that an experienced Mercedes mechanic would give a much more confident and accurate diagnosis. Just treat anything I say with a grain of salt